About a year and a half ago I met at work my today’s very best male friend (42 years old, I am 35). He is everything I like, and I rarely find someone I like, we became terrific friends quickly, started going out (only the 2 of us) very often, talking on the phone every day, met his family, he met mine, etc.

About two months after we met, I told him I wanted to try to be more than just friends; he replied saying that he was not at the right place with his mind to start a relationship because he was still struggling with his depression, but did say, maybe one day! I never said I was in love with him because I wasn’t.

We became even closer as friends, as he started to open up to myself a lot more. A lot of people assume that we are going out or like each other because we are so close.

Once more, eight months or so into the friendship, I said to him that I needed some distance because I was confused about his feeling towards me. He took me to meet his parents, close family, close friends, was doing much more than the ordinary very good opposite sex friend would do. I told him that he was stringing me along instead of being more open and say that he wanted something with me. Again, I did not say that I was in love with him because I was not sure about my feeling, but I did like him a lot and was open to trying.

He responded that his feeling towards me was not romantic, just a very dear friend. I always said I liked him a lot; he always said the same back. Since I am trying to see him as a brother, but it’s been hard!

A few weeks ago he told me that he started talking with an ex-girlfriend, but now they were just friends, that she was seeing someone else and that she had feelings for this someone. This last relationship of his was very short; she split up with him because she wanted to get pregnant soon but he didn’t want a child.

I was not able to cope with him talking about her anymore and told him that I wanted to avoid this conversation because it was causing me a lot of pain and I didn’t wish to mess up our friendship. I finally said that I had feelings towards him.

He was sweet and kind, explained to me that he was still feeling in love with her since they started talking again, and he said that he realized why he could not open his heart to anyone else. He wanted to try again with her.

Then I told him that I was sure that she never really liked him, etc. (because of many things he told me). He said that he would open his heart to her, just like I did to him, tell her his feelings so he could get a clear response from her, either way. And perhaps it would help him move on with his romantic life.

So, he did, and the obvious happened, she said that she is in love with this new guy and she wants to try with this other guy, it was a no.

Now, I am quite confused again, he doesn’t look distraught, for someone that is heartbroken, he is incredibly kind to me.

My question is, could he be making up this “event” of talking to her, to continue to string me along, or now have an excuse to make a move on me?

Or could he be just be telling me the truth? I just find it all a little too surreal, that he could be still in love with this woman after three years (no relationship since), going to tell her about his feelings, doing what I have just done to him (only one week apart).

I wanted this to work, in fact, a couple of times he did said how “deep” our friendship is, and the best couples usually come from best friends, that he never had this with anyone in his life.

I am puzzled because I liked him but assumed that when I declared my feelings, at last, he would take the next step.

He is a 43-year-old adult; he shouldn’t be playing with my feelings! He is a beautiful person that I don’t want out of my life, but I am struggling to move on with my personal life because I am in love with him and hope that he is also in love with me but taking his time due to his depression or whatever reason.

I might be overthinking this, but I’m a woman, so that’s natural, ha, ha.

Verry important – he is super shy, has trouble starting anything with girls. He is very sensitive and did say to me that he had many problems with being rejected in the past.

It took five years to get over his first girlfriend. He has only realized that he has always been ashamed to declare his feelings for someone. He said that is something he needs to work on.

I am on the chubby side (but have a beautiful face), and he is very skinny. His principal work with his therapist is on his self-esteem, he has significant issues. His father, two brothers and some of his friends were bullies.

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